Cesium carbonate → HCID 11523714, compound

HRID 1445823Notes

Reaction equation

HRID 1445823 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH3:21])=O)[N:12]=2)=[CH:4][CH:3]=1.Br.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:22][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:3][CH:4]=2)=[N:12][C:11]=1[CH2:13][CH2:14][N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 135487319HCID 135487319, compound

Product 1

HCID 11523714HCID 11523714, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(4-Hydroxy-phenyl)-5-methyl-oxazol-4-yl]-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone (See Example 56) (0.35 g, 1.2 mmol), 2-bromomethylpyridine hydrobromide (0.40 g, 1.6 mmol), and Cs2CO3 (1.4 g, 4.3 mmol) in DMF (5 mL) is stirred at room temperature overnight. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (2×), and the combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by flash chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2] to yield the title compound. MS (m/e): 378.3 (M+1)

Workup

  1. customThe mixture is partitioned between EtOAc and water
  2. extractionThe aqueous phase is extracted with EtOAc (2×)
  3. washthe combined organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2]

Sources & evidence

ORD record
ord-8509e5877ff445e2973707bc80254ca1
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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